RefMet Compound Details

RefMet ID, RefMet name, exact mass and formula
RefMet ID	RM0157860
RefMet name	GDP-L-fucose
Systematic name	{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid
Synonyms	PubChem Synonyms
Exact mass	589.082246 (neutral)	Calculate m/z: (Choose adduct) [M+H]+ [M+H-H2O]+ [M.]+ [M+2H]2+ [M+3H]3+ [M+4H]4+ [M+K]+ [M+2K]2+ [M+2K-H]+ [M+Na]+ [M+2Na]2+ [M+2Na-H]+ [M+Li]+ [M+2Li]2+ [M+NH4]+ [M.CH3]+ [M+Ag]+ [M+H+CH3OH]+ [M+H+CH3CN]+ [M+H+2CH3CN]+ [M+Na+CH3CN]+ [M.NaFormate+H]+ [M.NH4Formate+H]+ [M.TMSi]+ [M.tBuDMSi]+ [M+H-Hexose]+ [M+H-EtnP]+ [M+H-SerP]+ [M-H]- [M-H-H2O]- [M-CH3]- [M-2H]2- [M-3H]3- [M-4H]4- [M+Cl]- [M+OAc]- [M+Na-2H]- [M+K-2H]- [M.Formate]- [M.NaFormate-H]- [M.NH4Formate-H]- [M.F]- [M-H-Ser]- [M.HF2]- M(neutral)    View other RefMet entries with this exact (neutral) mass:   +/- 0.05 amu   +/- 0.1 amu   +/- 0.2 amu   +/- 0.5 amu
Formula	C16H25N5O15P2	View other entries in RefMet with this formula
Molecular descriptors
Molfile	37598 (Download molfile/View MW Metabolite Database details)
InChI	InChI=1S/C16H25N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20- 13(6)27/h3-5,7-11,14-15,22-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5+,7+,8+,9+,10+,11-,14+,15?/m0/s1
InChIKey	LQEBEXMHBLQMDB-QIXZNPMTSA-N	View other enantiomers/diastereomers of this metabolite in RefMet
SMILES	C[C@H]1[C@H]([C@H]([C@@H](C(O1)OP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@H](n2cnc3c2nc(N)[nH]c3=O)O1)O)O)O)O)O Run Tanimoto similarity search (with similarity coefficient >=0.6)
Chemical/Biochemical Classification
Super Class	Nucleic acids
Main Class	Purines
Sub Class	Purine rNDP
Distribution of GDP-L-fucose in NMDR studies
Species	Plot Species distribution
Sample source	Plot Sample source(tissue) distribution
Platform	Platform (MS/NMR) used for detection
Chromatography	Chromatography methods used for detection
Studies	NMDR Studies reporting GDP-L-fucose
External Links
Pubchem CID	135412609
ChEBI ID	17009
KEGG ID	C00325
HMDB ID	HMDB0001095
Chemspider ID	388350
Spectral data for GDP-L-fucose standards
MassBank(EU)	View MS spectra
Structural annotation level
Annotation level	1   (1:Known structure; 2:Known regiochemistry; 3:Partial structure; 4:Sum-composition)

Table of KEGG reactions in human pathways involving GDP-L-fucose

Rxn ID	KEGG Reaction	Enzyme
R01951	GTP + L-Fucose 1-phosphate <=> Diphosphate + GDP-L-fucose	GTP:beta-L-fucose-1-phosphate guanylyltransferase
R05692	GDP-L-fucose + NADP+ <=> GDP-4-dehydro-6-deoxy-D-mannose + NADPH + H+	GDP-L-fucose:NADP+ 4-oxidoreductase (3,5-epimerizing)

Table of KEGG human pathways containing GDP-L-fucose

Pathway ID	Human Pathway	# of reactions
hsa00051	Fructose and mannose metabolism	2
hsa00520	Amino sugar and nucleotide sugar metabolism	2